WO2016073351A1 - Procédés de récupération d'alcools - Google Patents

Procédés de récupération d'alcools Download PDF

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Publication number
WO2016073351A1
WO2016073351A1 PCT/US2015/058609 US2015058609W WO2016073351A1 WO 2016073351 A1 WO2016073351 A1 WO 2016073351A1 US 2015058609 W US2015058609 W US 2015058609W WO 2016073351 A1 WO2016073351 A1 WO 2016073351A1
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WIPO (PCT)
Prior art keywords
mol
stream
amount
certain embodiments
solvent
Prior art date
Application number
PCT/US2015/058609
Other languages
English (en)
Inventor
Kai Jürgen FISCHER
Pieter HUIZENGA
Wouter Koot
Martin MADERA
Original Assignee
Shell Oil Company
Shell Internationale Research Maatschappij B.V.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shell Oil Company, Shell Internationale Research Maatschappij B.V. filed Critical Shell Oil Company
Priority to BR112017009465A priority Critical patent/BR112017009465A2/pt
Priority to CN201580059622.4A priority patent/CN107001207A/zh
Priority to EP15794427.3A priority patent/EP3215245A1/fr
Priority to US15/523,618 priority patent/US20170305823A1/en
Priority to AU2015343391A priority patent/AU2015343391B2/en
Priority to EA201790975A priority patent/EA201790975A1/ru
Publication of WO2016073351A1 publication Critical patent/WO2016073351A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
    • C07C29/86—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0488—Flow sheets
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0492—Applications, solvents used
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/34—Separation; Purification; Stabilisation; Use of additives
    • C07C41/38—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment

Definitions

  • the present disclosure relates generally to methods of recovering alcohols from aqueous solutions. More specifically, in certain embodiments, the present disclosure relates to solvents useful for extracting alcohols from aqueous solutions and associated methods.
  • the extraction of hydrocarbons from deepwater oil and gas reservoirs may require the transportation of production streams from reservoirs to facilities for processing. Water, along with oil and gas, may be included in these production streams.
  • Water along with oil and gas, may be included in these production streams.
  • the system can enter the hydrate region where gas hydrates form. Gas hydrates are solids and, if formed, may plug the pipelines used to transport the production streams. Hydrates may also plug or cause malfunction of other units, such as valves, chokes, separators, heat exchangers, etc.
  • hydrate inhibitors added to the production streams.
  • An example of such a hydrate inhibitor is monoethylene glycol.
  • Another example of such a hydrate inhibitor is methanol.
  • the hydrate inhibitors added to the production streams may later be recovered from the production stream and recycled.
  • salt from the aqueous stream may accumulate in the glycol stream. After a certain amount of time, saturation level of the salt may reached and the salt may begin to precipitate out of solution. This may lead to scaling on equipment and may cause very costly shut downs of the production system.
  • the present disclosure relates generally to methods of recovering alcohols from aqueous solutions. More specifically, in certain embodiments, the present disclosure relates to solvents useful for extracting alcohols from aqueous solutions and associated methods.
  • the present disclosure provides a method of recovering an alcohol from an aqueous stream comprising: providing an aqueous stream comprising an alcohol; extracting at least a portion of the alcohol from the aqueous stream with a solvent to form an extracted solvent stream; extracting at least a portion of the alcohol from the extracted solvent stream to form an extracted aqueous stream; and recovering at least a portion of the alcohol from the extracted aqueous stream.
  • the present disclosure provides method of recovering an alcohol from an aqueous stream comprising: providing an aqueous stream comprising water and an alcohol; providing a solvent stream; combining the solvent stream and the aqueous stream to form an extracted solvent stream; providing a water stream; combining the extracted solvent stream with the water stream to form an extracted aqueous stream; and recovering at least a portion of the alcohol from the extracted aqueous stream.
  • the present disclosure provides a system for extracting an alcohol from an aqueous product stream comprising: a first extraction unit, a second extraction unit, and distillation unit.
  • Figure 1 is a process flow diagram in accordance with certain embodiments of the present disclosure.
  • the present disclosure relates generally to methods of recovering alcohols from aqueous solutions. More specifically, in certain embodiments, the present disclosure relates to solvents useful for extracting alcohols from aqueous solutions and associated methods.
  • the methods and systems described herein are novel approaches on how to prevent the accumulation of salt in glycol separation systems.
  • the methods discussed herein rely on extraction and then back extraction followed by distillation.
  • salt may continuously be rejected from a partial stream, thus keeping the salt concentration in the glycol loop at levels sufficient to prevent the precipitation of the salts in the distillation column or other equipment.
  • the present disclosure provides a method of recovering an alcohol from an aqueous stream comprising: providing an aqueous stream comprising an alcohol; extracting at least a portion of the alcohol from the aqueous stream with a solvent to form an extracted solvent stream; extracting at least a portion of the alcohol from the extracted solvent stream to form an extracted aqueous stream; and recovering at least a portion of the alcohol from the extracted aqueous stream.
  • the aqueous stream may be any aqueous stream comprising water and an alcohol.
  • the alcohol may comprise one or more monohydric alcohols, one or more polyhydric alcohols, or any combination thereof.
  • suitable polyhydric alcohols include polyols such as monoethylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, and glycerol.
  • the amount of water present in the aqueous stream may be an amount in the range of from 10 mol% to 99 mol%. In certain embodiments, the amount of water present in the aqueous stream may be an amount in the range of from 20 mol% to 90 mol%. In certain embodiments, the amount of water present in the aqueous stream may be an amount in the range of from 30 mol% to 85 mol%. In certain embodiments, the amount of water present in the aqueous stream may be an amount in the range of from 40 mol% to 80 mol%. In certain embodiments, the amount of water present in the aqueous stream may be an amount in the range of from 50 mol% to 70 mol%.
  • the amount of water present in the aqueous stream may be an amount in the range of from 70 mol% to 99 mol%. In certain embodiments, the amount of water present in the aqueous stream may be an amount in the range of from 80 mol% to 99 mol%. In certain embodiments, the amount of water present in the aqueous stream may be an amount in the range of from 90 mol% to 99 mol%.
  • the amount of alcohol present in the aqueous stream may be an amount in the range of from 1 mol% to 90 mol%. In certain embodiments, the amount of alcohol present in the aqueous stream may be an amount in the range of from 10 mol% to 80 mol%. In certain embodiments, the amount of alcohol present in the aqueous stream may be an amount in the range of from 15 mol% to 70 mol%. In certain embodiments, the amount of alcohol present in the aqueous stream may be an amount in the range of from 20 mol% to 60 mol%. In certain embodiments, the amount of alcohol present in the aqueous stream may be an amount in the range of from 30 mol% to 50 mol%.
  • the amount of alcohol present in the aqueous stream may be an amount in the range of from 1 mol% to 30 mol%. In certain embodiments, the amount of alcohol present in the aqueous stream may be an amount in the range of from 1 mol% to 20 mol%. In certain embodiments, the amount of alcohol present in the aqueous stream may be an amount in the range of from 1 mol% to 10 mol%.
  • the aqueous stream may further comprise one or more dissolved salts.
  • salts that may be included in the aqueous stream include sulfates, chlorides, and carbonates of potassium, sodium, magnesium, iron and calcium.
  • salts that are formed in corrosion processes, salts used as catalysts and salts formed in acid-base neutralization reactions may be present in the aqueous stream.
  • the dissolved salts may be present in the aqueous stream in an amount that is between zero and the salt solubility limit.
  • the salt may be present in an amount in the range of from about 0% to about 25% of the salt solubility limit.
  • the salt may be present in an amount in the range of from about 0.5% to about 20% of the salt solubility limit.
  • the salt may be present in an amount in the range of from about 1% to about 5% of the salt solubility limit
  • the aqueous stream may comprise a production stream.
  • the production stream may be a production stream from a subsea oil and/or gas well.
  • the production stream may comprise a mixture of oil, gas, water, and an alcohol.
  • the aqueous stream may comprise an aqueous stream separated from a production stream.
  • the amount of water present in the production stream may be an amount in the range of from 0% to about 50% by weight of the production stream. In other embodiments, the amount of water present in the production stream may be in an amount in the range of from about 5% to about 50% by weight of the production stream. In other embodiments, the water may be present in the production stream in an amount in the range of from about 10% to about 25% by weight of the production stream.
  • the oil and gas may be present in the production stream in an amount that is between the minimum and maximum solubility of oil and gas in the production stream at given conditions.
  • the amount of oil and gas present in the production stream may be an amount in the range of from about 0 mol% to 25 mol%.
  • the amount of oil and gas present in the production stream may be an amount in the range of from about 0.5 mol% to about 15 mol%.
  • the amount of oil and gas present in the production stream may be an amount in the range of from about 1 mol% to about 5 mol%.
  • the dissolved salts may be present in the production stream in an amount that is between zero and the salt solubility limit.
  • the salt may be present in an amount in the range of from about 0% to about 25% of the salt solubility limit.
  • the salt may be present in an amount in the range of from about 0.5% to about 20% of the salt solubility limit.
  • the salt may be present in an amount in the range of from about 1% to about 5% of the salt solubility limit.
  • the production stream may further comprise one or more hydrate forming gases, gases in dense phase, or hydrate forming liquid hydrocarbons.
  • hydrate forming gases examples include methane, ethane, propane, butane, carbon dioxide and hydrogen sulfide.
  • the amount of hydrate forming gas in the production stream, or the amount of hydrate forming liquid hydrocarbon may be from 0 mol% to 100 mol% based upon the amount of water in the production stream, and typically may be from 25 mol% to 100 mol%.
  • the alcohol may be present in, or added to, the production stream in an amount sufficient to prevent the formation of hydrates in the production stream as it is transported from the subsea oil and gas well.
  • the amount of alcohol necessary to prevent the formation of hydrates may depend on several factors including the pressure of the production stream, the temperature of the production stream, the water content of the production stream, the salinity of the production stream, the concentration of any additives injected in the production stream, and the concentration of hydrate forming gas in the production stream.
  • the amount of alcohol present in the production stream may be in an amount from 0 mol% to 50 mol% of the water present in the production stream. In other embodiments, the amount of alcohol present in the production stream may be in an amount from 10 mol% to 25 mol% of the water present in the production stream.
  • providing an aqueous stream comprising an alcohol may further comprise separating the aqueous stream into a first portion and a second portion.
  • the first portion may comprise up to 50% of the aqueous stream.
  • the first portion may comprise between 5% and 40% of the aqueous stream.
  • the first portion may comprise between 10% and 30% of the aqueous stream.
  • extracting at least a portion of the alcohol from the aqueous stream with a solvent to form an extracted solvent stream may comprise extracting at least a portion of the alcohol from the first portion of the aqueous stream. In certain embodiments, extracting at least a portion of the alcohol from the aqueous stream with a solvent to form an extracted solvent stream may further comprise forming a spent aqueous stream.
  • extracting the alcohol from the aqueous stream, or the first portion thereof, with a solvent to form an extracted solvent stream may comprise combining the aqueous stream, or the first portion thereof, with a solvent or a solvent stream.
  • the aqueous stream, or the first portion thereof may be combined with a solvent or a solvent stream within an extraction unit or mixer/settler arrangement.
  • extracting at least a portion of the alcohol from the aqueous stream with a solvent to form an extracted solvent stream may further comprise forming a spent aqueous stream.
  • the solvent stream may comprise a solvent and water.
  • the amount of solvent present in the solvent stream may be an amount in the range of from 50 mol% to 99 mol%. In certain embodiments, the amount of solvent present in the solvent stream may be an amount in the range of from 60 mol% to 97.5 mol%. In certain embodiments, the amount of solvent present in the solvent stream may be an amount in the range of from 70 mol% to 95 mol%. In certain embodiments, the amount of solvent present in the solvent stream may be an amount in the range of from 80 mol% to 90 mol%. In certain embodiments, the amount of solvent present in the solvent stream may be an amount in the range of from 90 mol% to 99 mol%.
  • the amount of solvent present in the solvent stream may be an amount in the range of from 95 mol% to 99 mol%.
  • concentration of solvent in the solvent stream may depend upon the type of solvent used, the temperature of the solvent stream, and the particular extraction equipment used.
  • the amount of water present in the solvent stream may be an amount in the range of from 0.01 mol% to 50 mol%. In certain embodiments, the amount of water present in the solvent stream may be an amount in the range of from 2.5 mol% to 40 mol%. In certain embodiments, the amount of water present in the solvent stream may be an amount in the range of from 5 mol% to 30 mol%. In certain embodiments, the amount of water present in the solvent stream may be an amount in the range of from 10 mol% to 20 mol%. In certain embodiments, the amount of water present in the solvent stream may be an amount in the range of from 1 mol% to 10 mol%.
  • the amount of water present in the solvent stream may be an amount in the range of from 1 mol% to 5 mol%. In certain embodiments, the amount of water present in the solvent stream may be an amount in the range of from 0.01 mol% to 2.5 mol%.
  • the solvent stream may further comprise an alcohol.
  • the alcohol may comprise any alcohol discussed above or any combination thereof.
  • the amount of alcohol present in the solvent stream may be an amount in the range of from 0.01 mol% to 5 mol%. In certain embodiments, the amount of alcohol present in the solvent stream may be an amount in the range of from 0.05 mol% to 2.5 mol%. In certain embodiments, the amount of alcohol present in the solvent stream may be an amount in the range of from 0.1 mol% to 1 mol%. In certain embodiments, the amount of alcohol present in the solvent stream may be an amount in the range of from 0.05 mol% to 0.5 mol%.
  • the solvent may comprise a solvent that is not fully miscible with water. In certain embodiments the solvent may comprise a solvent that has a higher affinity for alcohol than water. In certain embodiments, the solvent may comprise an amine solvent. In certain embodiments, the solvent may comprise a tertiary amine solvent. In certain embodiments, the solvent may comprise dimethylcyclohexylamine, methylcyclohexylamine, methyl piperidine, triethylamine, tripropylamine, or any combination thereof.
  • the extraction unit may comprise of a multistage extraction column.
  • the column may be equipped with internals such as trays, structured packing or moving internals in order to ensure increase the interface area to facilitate mass transfer between the phases.
  • the extraction equipment may be a single mixer or settler or several serial mixers and/or settlers.
  • the extraction unit may be operated at a temperature in the range of from 15°C to 90°C. In certain embodiments the extraction unit may be operated at a temperature in the range of from 20°C to 80°C. In other embodiments, the extraction unit may be operated at a temperature in the range of from 50°C to 70°C.
  • the alcohol present in the aqueous stream, or first portion thereof may be extracted from the aqueous stream, or first portion thereof.
  • a solvent phase may be formed within the extraction unit, wherein the solvent phase comprises a major portion of the alcohol present in the aqueous stream, or first portion thereof, and minor portions of the water and salt present in the aqueous stream, or first portion thereof.
  • an aqueous phase may be formed within the extraction unit, wherein the aqueous phase comprises a minor portion of the alcohol present in the aqueous stream, or first portion thereof, and major portions of the water and salt present in the aqueous stream, or first portion thereof.
  • the aqueous phase may leave the extraction unit as a spent aqueous stream.
  • the spent aqueous stream may comprise a major portion of the water from the aqueous stream, or first portion thereof.
  • the amount of water present in the spent aqueous stream may be an amount in the range of from 50 mol% to 99 mol%.
  • the amount of water present in the spent aqueous stream may be an amount in the range of from 60 mol% to 97.5 mol%.
  • the amount of water present in the spent aqueous stream may be an amount in the range of from 70 mol% to 95 mol%.
  • the amount of water present in the spent aqueous stream may be an amount in the range of from 80 mol% to 90 mol%. In certain embodiments, the amount of water present in the spent aqueous stream may be an amount in the range of from 90 mol% to 99 mol%. In certain embodiments, the amount of water present in the spent aqueous stream may be an amount in the range of from 95 mol% to 99 mol%.
  • the spent aqueous stream may further comprise a minor portion of the solvent from the solvent stream.
  • the amount of solvent present in the spent aqueous stream may be an amount in the range of from 0.01 mol% to 10 mol%. In certain embodiments, the amount of solvent present in the spent aqueous stream may be an amount in the range of from 0.1 mol% to 5 mol%. In certain embodiments, the amount of solvent present in the spent aqueous stream may be an amount in the range of from 1 mol% to 2.5 mol%. In certain embodiments, the amount of solvent present in the spent aqueous stream may be an amount in the range of from 0.01 mol% to 1 mol%.
  • the amount of solvent present in the spent aqueous stream may be an amount in the range of from 0.1 mol% to 1 mol%. In certain embodiments, the amount of solvent present in the spent aqueous stream may be an amount in the range of from 2.5 mol% to 10 mol%.
  • the spent aqueous stream may further comprise a minor portion of the alcohol from the aqueous stream, or first portion thereof.
  • the amount of alcohol present in the spent aqueous stream may be an amount in the range of from 0.01 mol% to 10 mol%.
  • the amount of alcohol present in the spent aqueous stream may be an amount in the range of from 0.1 mol% to 5 mol%.
  • the amount of alcohol present in the spent aqueous stream may be an amount in the range of from 1 mol% to 2.5 mol%.
  • the amount of alcohol present in the spent aqueous stream may be an amount in the range of from 0.01 mol% to 1 mol%.
  • the amount of alcohol present in the spent aqueous stream may be an amount in the range of from 0.1 mol% to 1 mol%. In certain embodiments, the amount of alcohol present in the spent aqueous stream may be an amount in the range of from 2.5 mol% to 10 mol%.
  • the spent aqueous stream may further comprise a major portion of the salt present in the aqueous stream, or first portion thereof.
  • the spent aqueous stream may comprise 60% to 100% of the salt present in the aqueous stream or first portion thereof.
  • the spent aqueous stream may comprise 70% to 100% of the salt present in the aqueous stream or first portion thereof.
  • the spent aqueous stream may comprise 80% to 100% of the salt present in the aqueous stream or first portion thereof.
  • the spent aqueous stream may comprise 90% to 100% of the salt present in the aqueous stream or first portion thereof.
  • the spent aqueous stream may comprise 95% to 100% of the salt present in the aqueous stream or first portion thereof. In certain embodiments, the spent aqueous stream may comprise 97.5% to 100% of the salt present in the aqueous stream or first portion thereof. In certain embodiments, the spent aqueous stream may comprise 99% to 100% of the salt present in the aqueous stream or first portion thereof. In certain embodiments, the spent aqueous stream may comprise 99.9% to 100% of the salt present in the aqueous stream or first portion thereof.
  • the spent aqueous stream may be disposed of.
  • the solvent in the spent aqueous stream may be separated from the spent aqueous stream in a stripper or flash drum.
  • the spent aqueous stream may be sent to a water purification unit, such as a biological or chemical water treatment plant.
  • the solvent phase may leave the extraction unit as an extracted solvent stream.
  • the extracted solvent stream may comprise a minor portion of the water from the aqueous stream, or first portion thereof.
  • the amount of water present in the extracted solvent stream may be an amount in the range of from 1 mol% to 50 mol%.
  • the amount of water present in the extracted solvent stream may be an amount in the range of from 2.5 mol% to 40 mol%.
  • the amount of water present in the spent extracted solvent stream may be an amount in the range of from 5 mol% to 30 mol%.
  • the amount of water present in the extracted solvent stream may be an amount in the range of from 10 mol% to 20 mol%.
  • the amount of water present in the extracted solvent stream may be an amount in the range of from 1 mol% to 10 mol%. In certain embodiments, the amount of water present in the extracted solvent stream may be an amount in the range of from 1 mol% to 5 mol%.
  • the extracted solvent stream may further comprise a major portion of the solvent from the solvent stream.
  • the amount of solvent present in the extracted solvent stream may be an amount in the range of from 50 mol% to 99 mol%. In certain embodiments, the amount of solvent present in the extracted solvent stream may be an amount in the range of from 60 mol% to 90 mol%. In certain embodiments, the amount of solvent present in the spent aqueous stream may be an amount in the range of from 70 mol% to 80 mol%. In certain embodiments, the amount of solvent present in the extracted solvent stream may be an amount in the range of from 60 mol% to 70 mol%.
  • the amount of solvent present in the extracted solvent stream may be an amount in the range of from 70 mol% to 90 mol%. In certain embodiments, the amount of solvent present in the extracted solvent stream may be an amount in the range of from 80 mol% to 99 mol%.
  • the extracted solvent stream may further comprise a major portion of the alcohol from the aqueous stream, or first portion thereof.
  • the amount of alcohol present in the extracted solvent stream may be an amount in the range of from 1 mol% to 50 mol%. In certain embodiments, the amount of alcohol present in the extracted solvent stream may be an amount in the range of from 10 mol% to 40 mol%. In certain embodiments, the amount of alcohol present in the extracted solvent stream may be an amount in the range of from 10 mol% to 30 mol%. In certain embodiments, the amount of alcohol present in the extracted solvent stream may be an amount in the range of from 20 mol% to 30 mol%.
  • the amount of alcohol present in the extracted solvent stream may be an amount in the range of from 30 mol% to 40 mol%. In certain embodiments, the amount of alcohol present in the extracted solvent stream may be an amount in the range of from 1 mol% to 20 mol%. In certain embodiments, the amount of alcohol present in the extracted solvent stream may be an amount in the range of from 20 mol% to 50 mol%.
  • the extracted solvent stream may further comprise a minor portion of the salt present in the aqueous stream, or first portion thereof.
  • the extracted solvent stream may comprise 0% to 40% of the salt present in the aqueous stream or first portion thereof.
  • the extracted solvent stream may comprise 0% to 30% of the salt present in the aqueous stream or first portion thereof.
  • the extracted solvent stream may comprise 0% to 20% of the salt present in the aqueous stream or first portion thereof.
  • the extracted solvent stream may comprise 0% to 10% of the salt present in the aqueous stream or first portion thereof.
  • the extracted solvent stream may comprise 0% to 5% of the salt present in the aqueous stream or first portion thereof. In certain embodiments, the extracted solvent stream may comprise 0% to 2.5% of the salt present in the aqueous stream or first portion thereof. In certain embodiments, the extracted solvent stream may comprise 0% to 1% of the salt present in the aqueous stream or first portion thereof. In certain embodiments, the extracted solvent stream may comprise 0.1% to 1% of the salt present in the aqueous stream or first portion thereof.
  • extracting at least a portion of the alcohol from the extracted solvent stream to form an extracted aqueous stream may comprise extracting at least a portion of the alcohol from the extracted solvent stream. In certain embodiments, extracting at least a portion of the alcohol from the extracted solvent stream to form an extracted aqueous stream may further comprise forming a spent solvent stream.
  • extracting at least a portion of the alcohol from the extracted solvent stream to form an extracted aqueous stream may comprise combining the extracted solvent stream with water or water stream.
  • the extracted solvent stream may be combined with water or a water stream within an extraction unit.
  • extracting at least a portion of the alcohol from the extracted solvent stream with water to form an extracted aqueous stream may further comprise forming a spent solvent stream.
  • the water stream may comprise water and traces of solvent and alcohol.
  • the traces of solvent and alcohol may be below 1%.
  • the extraction unit may comprise an extraction column.
  • the extraction column may be equipped with trays.
  • the extraction column may be equipped with structured packing or rotating internals.
  • the extraction unit may comprise one or more mixers and/or settlers.
  • the extraction unit may be operated at a temperature in the range of from 100°C to about 150°C.
  • the alcohol present in the extracted solvent stream may be extracted from the extracted solvent stream.
  • a solvent phase may be formed within the extraction unit, wherein the solvent phase comprises a major portion of the solvent in the extracted solvent stream and a minor portion of the alcohol from the extracted solvent stream and the water from the water stream.
  • an aqueous phase may be formed within the extraction unit, wherein the aqueous phase comprises major portions of the alcohol present in the extracted solvent stream and water from the water stream and a minor portion of the solvent from the extracted solvent stream.
  • the aqueous phase may leave the extraction unit as an extracted aqueous stream.
  • the extracted aqueous stream may comprise a major portion of the water from the water stream.
  • the amount of water present in the extracted aqueous stream may be an amount in the range of from 50 mol% to 90 mol%.
  • the amount of water present in the extracted aqueous stream may be an amount in the range of from 60 mol% to 80 mol%.
  • the amount of water present in the extracted aqueous stream may be an amount in the range of from 70 mol% to 80 mol%.
  • the amount of water present in the extracted aqueous stream may be an amount in the range of from 80 mol% to 90 mol%.
  • the amount of water present in the extracted aqueous stream may be an amount in the range of from 50 mol% to 80 mol%. In certain embodiments, the amount of water present in the extracted aqueous stream may be an amount in the range of from 60 mol% to 70 mol%.
  • the extracted aqueous stream may comprise a minor portion of the solvent from the extracted solvent stream.
  • the amount of solvent present in the extracted aqueous stream may be an amount in the range of from 0.01 mol% to 10 mol%. In certain embodiments, the amount of solvent present in the extracted aqueous stream may be an amount in the range of from 0.1 mol% to 5 mol%. In certain embodiments, the amount of solvent present in the extracted aqueous stream may be an amount in the range of from 1 mol% to 2.5 mol%. In certain embodiments, the amount of solvent present in the extracted aqueous stream may be an amount in the range of from 0.01 mol% to 1 mol%.
  • the amount of solvent present in the extracted aqueous stream may be an amount in the range of from 0.1 mol% to 1 mol%. In certain embodiments, the amount of solvent present in the extracted aqueous stream may be an amount in the range of from 2.5 mol% to 10 mol%.
  • the extracted aqueous stream may comprise a major portion of the alcohol from the extracted solvent stream.
  • the amount of alcohol present in the extracted aqueous stream may be an amount in the range of from 10 mol% to 50 mol%.
  • the amount of alcohol present in the extracted aqueous stream may be an amount in the range of from 20 mol% to 50 mol%.
  • the amount of alcohol present in the extracted aqueous stream may be an amount in the range of from 20 mol% to 40 mol%.
  • the amount of alcohol present in the extracted aqueous stream may be an amount in the range of from 30 mol% to 50 mol%.
  • the amount of alcohol present in the extracted aqueous stream may be an amount in the range of from 30 mol% to 40 mol%. In certain embodiments, the amount of alcohol present in the extracted aqueous stream may be an amount in the range of from 40 mol% to 50 mol%.
  • the extracted aqueous stream may further comprise a major portion of the salt present in the extracted solvent stream.
  • the extracted aqueous stream may comprise 60% to 100% of the salt present in the extracted solvent stream.
  • the extracted aqueous stream may comprise 70% to 100% of the salt present in the extracted solvent stream.
  • the extracted aqueous stream may comprise 80% to 100% of the salt present in the extracted solvent stream.
  • the extracted aqueous stream may comprise 90% to 100% of the salt present in the extracted solvent stream.
  • the extracted aqueous stream may comprise a negligible amount of salt.
  • the solvent phase may leave the extraction unit as a spent solvent stream.
  • the spent solvent stream may comprise a major portion of the solvent from the extracted solvent stream.
  • the amount of solvent present in the spent solvent stream may be an amount in the range of from 80 mol% to 99 mol%.
  • the amount of solvent present in the spent solvent stream may be an amount in the range of from 80 mol% to 95 mol%.
  • the amount of solvent present in the spent solvent stream may be an amount in the range of from 90 mol% to 99 mol%.
  • the amount of solvent present in the spent solvent stream may be an amount in the range of from 85 mol% to 90 mol%.
  • the amount of solvent present in the spent solvent stream may be an amount in the range of from 90 mol% to 95 mol%. In certain embodiments, the amount of solvent present in the spent solvent stream may be an amount in the range of from 85 mol% to 90 mol%.
  • the spent solvent stream may comprise a minor portion of the water from the extracted solvent stream.
  • the amount of water present in the spent solvent stream may be an amount in the range of from 0.01 mol% to 20 mol%. In certain embodiments, the amount of water present in the spent solvent stream may be an amount in the range of from 0.1 mol% to 10 mol%. In certain embodiments, the amount of water present in the spent solvent stream may be an amount in the range of from 1 mol% to 10 mol%. In certain embodiments, the amount of water present in the spent solvent stream may be an amount in the range of from 1 mol% to 5 mol%.
  • the amount of water present in the spent solvent stream may be an amount in the range of from 2.5 mol% to 5 mol%. In certain embodiments, the amount of water present in the spent solvent stream may be an amount in the range of from 2.5 mol% to 10 mol%.
  • the spent solvent stream may comprise a minor portion of the alcohol from the extracted solvent stream.
  • the amount of alcohol present in the spent solvent stream may be an amount in the range of from 0 mol% to 5 mol%.
  • the amount of alcohol present in the spent solvent stream may be an amount in the range of from 0.01 mol% to 2.5 mol%.
  • the amount of alcohol present in the spent solvent stream may be an amount in the range of from 0.1 mol% to 1 mol%.
  • the amount of alcohol present in the spent solvent stream may be an amount in the range of from 0.25 mol% to 0.5 mol%.
  • the extracted aqueous stream may comprise a minor portion of the salt present in the extracted solvent stream.
  • the spent solvent stream may comprise 0% to 40% of the salt present in the extracted solvent stream.
  • the spent solvent stream may comprise 0% to 30% of the salt present in the extracted solvent stream.
  • the spent solvent stream may comprise 0% to 20% of the salt present in the extracted solvent stream.
  • the spent solvent stream may comprise 0% to 10% of the salt present in the extracted solvent stream.
  • the extracted aqueous stream may comprise a negligible amount of salt.
  • the spent solvent stream or a portion thereof may be recycled as the solvent stream.
  • recovering at least a portion of the alcohol from the extracted aqueous stream may comprise recovering at least a portion of the alcohol from the extracted aqueous stream and the second portion of the aqueous stream. In certain embodiments, recovering at least a portion of the alcohol from the extracted aqueous stream may comprise combining the extracted aqueous stream with the second portion of the aqueous stream to form a combined aqueous stream and recovering at least a portion of the alcohol from the combined aqueous stream. In certain embodiments, recovering at least a portion of the alcohol from extracted aqueous stream may be accomplished by performing distillation.
  • recovering the alcohol from the extracted aqueous stream, the second portion of the aqueous stream, and/or the combined aqueous stream may comprise forming a recovered alcohol stream.
  • recovering the alcohol from the extracted aqueous stream, the second portion of the aqueous stream, and/or the combined aqueous stream may comprise forming a recovered aqueous stream.
  • the step of recovering the alcohol from the extracted aqueous stream, the second portion of the aqueous stream, and/or the combined aqueous stream may be performed within a distillation unit.
  • the distillation unit may comprise a rectification column.
  • the distillation column may be equipped with a reboiler.
  • the reboiler may be a kettle type or a thermosyphon type reboiler.
  • the distillation unit may be operated at a temperature in the range of from 90°C to 160°C.
  • a major portion of the alcohol, along with a minor portion of the water, present in the extracted aqueous stream, the second portion of the aqueous stream, and/or the combined aqueous stream may leave the distillation unit as a recovered alcohol stream.
  • the amount of water present in the recovered alcohol stream may be an amount in the range of from 0 mol% to 50 mol%. In certain embodiments, the amount of water present in the recovered alcohol stream may be an amount in the range of from 0 mol% to 40 mol%. In certain embodiments, the amount of water present in the recovered alcohol stream may be an amount in the range of from 5 mol% to 40 mol%. In certain embodiments, the amount of water present in the recovered alcohol stream may be an amount in the range of from 10 mol% to 40 mol%. In certain embodiments, the amount of water present in the recovered alcohol stream may be an amount in the range of from 20 mol% to 40 mol%. In certain embodiments, the amount of water present in the recovered alcohol stream may be an amount in the range of from 30 mol% to 40 mol%.
  • the amount of solvent present in the recovered alcohol stream may be an amount in the range of from 0.01 mol% to 5 mol%. In certain embodiments, the amount of solvent present in the recovered alcohol stream may be an amount in the range of from 0.1 mol% to 2.5 mol%. In certain embodiments, the amount of solvent present in the recovered alcohol stream may be an amount in the range of from 0.1 mol% to 1 mol%. In certain embodiments, the amount of solvent present in the recovered alcohol stream may be an amount in the range of from 0.01 mol% to 0.5 mol%. In certain embodiments, the amount of solvent present in the recovered alcohol stream may be an amount in the range of from 0.5 mol% to 1 mol%. In certain embodiments, the amount of solvent present in the recovered alcohol stream may be an amount in the range of from 0.25 mol% to 0.5 mol%.
  • the amount of alcohol present in the recovered alcohol stream may be an amount in the range of from 50 mol% to 99 mol%. In certain embodiments, the amount of alcohol present in the recovered alcohol stream may be an amount in the range of from 60 mol% to 99 mol%. In certain embodiments, the amount of alcohol present in the recovered alcohol stream may be an amount in the range of from 70 mol% to 95 mol%. In certain embodiments, the amount of alcohol present in the recovered alcohol stream may be an amount in the range of from 80 mol% to 90 mol%. In certain embodiments, the amount of alcohol present in the recovered alcohol stream may be an amount in the range of from 85 mol% to 95 mol%. In certain embodiments, the amount of alcohol present in the recovered alcohol stream may be an amount in the range of from 50 mol% to 80 mol%.
  • a major portion of the water, along with a minor portion of the alcohol, present in the extracted aqueous stream, the second portion of the aqueous stream, and/or the combined aqueous stream may leave the distillation unit as a recovered aqueous stream.
  • the amount of water present in the recovered aqueous stream may be an amount in the range of from 80 mol% to 99.9 mol%. In certain embodiments, the amount of water present in the recovered aqueous stream may be an amount in the range of from 85 mol% to 99.9 mol%. In certain embodiments, the amount of water present in the recovered aqueous stream may be an amount in the range of from 90 mol% to 95 mol%. In certain embodiments, the amount of water present in the recovered aqueous stream may be an amount in the range of from 90 mol% to 99.9 mol%.
  • the amount of water present in the recovered aqueous stream may be an amount in the range of from 95 mol% to 99.9 mol%. In certain embodiments, the amount of water present in the recovered aqueous stream may be an amount in the range of from 85 mol% to 95 mol%. In certain embodiments, the amount of water present in the recovered aqueous stream may be an amount in the range of from 85 mol% to 90 mol%.
  • the amount of solvent present in the recovered aqueous stream may be an amount in the range of from 0.01 mol% to 10 mol%. In certain embodiments, the amount of solvent present in the recovered aqueous stream may be an amount in the range of from 0.01 mol% to 5 mol%. In certain embodiments, the amount of solvent present in the recovered aqueous stream may be an amount in the range of from 0.1 mol% to 2.5 mol%. In certain embodiments, the amount of solvent present in the recovered aqueous stream may be an amount in the range of from 0.01 mol% to 1 mol%.
  • the amount of solvent present in the recovered aqueous stream may be an amount in the range of from 0.5 mol% to 1 mol%. In certain embodiments, the amount of solvent present in the recovered aqueous stream may be an amount in the range of from 0.25 mol% to 0.5 mol%.
  • the amount of alcohol present in the recovered aqueous stream may be an amount in the range of from 0.01 mol% to 10 mol%. In certain embodiments, the amount of alcohol present in the recovered aqueous stream may be an amount in the range of from 0.01 mol% to 5 mol%. In certain embodiments, the amount of alcohol present in the recovered aqueous stream may be an amount in the range of from 0.1 mol% to 2.5 mol%. In certain embodiments, the amount of alcohol present in the recovered aqueous stream may be an amount in the range of from 0.01 mol% to 1 mol%.
  • the amount of alcohol present in the recovered aqueous stream may be an amount in the range of from 0.5 mol% to 1 mol%. In certain embodiments, the amount of alcohol present in the recovered aqueous stream may be an amount in the range of from 0.25 mol% to 0.5 mol%.
  • the recovered aqueous stream may be disposed of. In certain embodiments, the recovered aqueous stream, or a portion thereof, may be recycled as the water stream.
  • the present disclosure provides a system for extracting an alcohol from an aqueous product stream comprising: a first extraction unit, a second extraction unit, and distillation unit.
  • a system for extracting an alcohol from an aqueous product stream comprising: a first extraction unit, a second extraction unit, and distillation unit.
  • Figure 1 illustrates a glycol removal system
  • first extraction unit 1100 may comprise any extraction unit discussed above.
  • second extraction unit 1200 may comprise any unit discussed above.
  • distillation unit 1300 may comprise any distillation unit discussed above.
  • first extraction unit 1100 As can be seen in Figure 1, aqueous stream 1101 and solvent stream 1102 may be supplied to first extraction unit
  • aqueous stream 1101 may comprise any aqueous stream discussed above.
  • solvent stream 1102 may comprise any solvent stream discussed above.
  • alcohol may be extracted from aqueous stream 1101 within first extraction unit 1100 by solvent stream 1102 thereby forming extracted solvent stream 1103 and spent aqueous stream 1104.
  • spent aqueous stream 1104 may comprise any spent aqueous stream discussed above.
  • extracted solvent stream may comprise any spent aqueous stream discussed above.
  • 1103 may comprise any extracted solvent stream discussed above.
  • extracted solvent stream 1103 and water stream 1105 may be supplied to second extraction unit 1200.
  • water stream 1105 may comprise any water stream discussed above.
  • alcohol may be extracted from extracted solvent stream 1103 by water stream 1105 thereby forming solvent stream 1102 and extracted aqueous stream 1106.
  • extracted aqueous stream 1106 may comprise any extracted aqueous stream discussed above.
  • solvent stream 1102 may comprise any spent solvent stream discussed above.
  • extracted aqueous stream 1106 may be supplied to directly to distillation unit 1300.
  • aqueous stream 1107 may be added to aqueous stream 1106 before it is supplied to distillation unit 1300.
  • aqueous stream 1101 may comprise a first portion of aqueous stream 1108 and aqueous stream 1107 may comprise a second portion of aqueous stream 1108.
  • aqueous streams 1107 and 1108 may have the same compositional make up of aqueous stream
  • aqueous stream 1107 and 1108 may comprise any aqueous stream discussed above, and any portion thereof.
  • alcohol may be distilled from extracted aqueous stream 1106 within distillation unit 1300 thereby forming recovered aqueous stream 1109 and recovered alcohol stream 1110.
  • recovered aqueous stream 1109 may comprise any recovered aqueous stream discussed above.
  • recovered alcohol stream 1110 may comprise any recovered alcohol stream discussed above.
  • a portion of recovered aqueous stream 1109 may be recycled as water stream 1105.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Extraction Or Liquid Replacement (AREA)

Abstract

L'invention concerne un procédé de récupération d'un alcool à partir d'un flux aqueux, le procédé consistant à : fournir un flux aqueux comprenant un alcool; extraire au moins une partie de l'alcool du flux aqueux à l'aide d'un solvant pour former un flux de solvant extrait; extraire du flux de solvant extrait au moins une partie du solvant pour former un flux aqueux extrait; et récupérer au moins une partie de l'alcool du flux aqueux extrait.
PCT/US2015/058609 2014-11-04 2015-11-02 Procédés de récupération d'alcools WO2016073351A1 (fr)

Priority Applications (6)

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BR112017009465A BR112017009465A2 (pt) 2014-11-04 2015-11-02 processos para recuperar álcoois
CN201580059622.4A CN107001207A (zh) 2014-11-04 2015-11-02 用于回收醇的方法
EP15794427.3A EP3215245A1 (fr) 2014-11-04 2015-11-02 Procédés de récupération d'alcools
US15/523,618 US20170305823A1 (en) 2014-11-04 2015-11-02 Process for reclaiming alcohols
AU2015343391A AU2015343391B2 (en) 2014-11-04 2015-11-02 Processes for reclaiming alcohols
EA201790975A EA201790975A1 (ru) 2014-11-04 2015-11-02 Способы извлечения спиртов

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US201462074992P 2014-11-04 2014-11-04
US62/074,992 2014-11-04

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AU (1) AU2015343391B2 (fr)
BR (1) BR112017009465A2 (fr)
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CN113966322A (zh) * 2019-03-08 2022-01-21 艾克福特士技术有限公司 一种醇回收溶液及其使用方法
CN114630817A (zh) 2019-09-24 2022-06-14 爱荷华谷类推广协会 用于操作连续未调制多催化步骤工艺的方法
US11319269B2 (en) 2020-09-24 2022-05-03 Iowa Corn Promotion Board Continuous processes for the selective conversion of aldohexose-yielding carbohydrate to ethylene glycol using low concentrations of retro-aldol catalyst
US11680031B2 (en) 2020-09-24 2023-06-20 T. EN Process Technology, Inc. Continuous processes for the selective conversion of aldohexose-yielding carbohydrate to ethylene glycol using low concentrations of retro-aldol catalyst
CN113090255B (zh) * 2021-03-11 2022-06-14 广州海洋地质调查局 一种天然气水合物伴生自生碳酸盐岩晶格硫酸盐的提取方法

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WO1995011876A1 (fr) * 1993-10-29 1995-05-04 Elf Aquitaine Production Procede de purification d'une solution glycolique
US20040222153A1 (en) * 2003-05-06 2004-11-11 A. E. Staley Manufacturing Co. Process for producing 1, 3-propanediol
US20090171129A1 (en) * 2007-12-27 2009-07-02 Gevo, Inc. Recovery of higher alcohols from dilute aqueous solutions
WO2013168077A1 (fr) * 2012-05-11 2013-11-14 Aker Process Systems As Élimination de sel d'acide carboxylique pendant la récupération d'un inhibiteur d'hydrate
US20140039667A1 (en) 2011-02-11 2014-02-06 Savoye Station for preparing orders comprising at least one shaft for vertically accumulating and sequentially dispensing containers
WO2014193889A1 (fr) * 2013-05-31 2014-12-04 Shell Oil Company Récupération de glycol avec extraction par solvant

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WO1995011876A1 (fr) * 1993-10-29 1995-05-04 Elf Aquitaine Production Procede de purification d'une solution glycolique
US20040222153A1 (en) * 2003-05-06 2004-11-11 A. E. Staley Manufacturing Co. Process for producing 1, 3-propanediol
US20090171129A1 (en) * 2007-12-27 2009-07-02 Gevo, Inc. Recovery of higher alcohols from dilute aqueous solutions
US20140039667A1 (en) 2011-02-11 2014-02-06 Savoye Station for preparing orders comprising at least one shaft for vertically accumulating and sequentially dispensing containers
WO2013168077A1 (fr) * 2012-05-11 2013-11-14 Aker Process Systems As Élimination de sel d'acide carboxylique pendant la récupération d'un inhibiteur d'hydrate
WO2014193889A1 (fr) * 2013-05-31 2014-12-04 Shell Oil Company Récupération de glycol avec extraction par solvant

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US20170305823A1 (en) 2017-10-26
AU2015343391A1 (en) 2017-04-27
AU2015343391B2 (en) 2018-08-02
BR112017009465A2 (pt) 2017-12-19
EP3215245A1 (fr) 2017-09-13
CN107001207A (zh) 2017-08-01
EA201790975A1 (ru) 2017-09-29

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